Common Deployment Issues and Fixes

Overview

Every Copilot deployment hits bumps. The good news is that the most common issues are predictable and fixable. Knowing the top problems and their solutions before they happen saves you days of troubleshooting and keeps user confidence high.

This video covers the deployment issues that government IT teams encounter most frequently—from licensing mistakes to network blocks to content access gaps—with practical fixes for each.

What You’ll Learn

• Licensing Issues: Missing licenses, propagation delays, and service plan conflicts
• Client Problems: Unsupported versions, update channel mismatches, and platform differences
• Network Blocks: Proxy, firewall, SSL inspection, and government-specific endpoint errors
• Policy Conflicts: Conditional Access, tenant settings, and app-level policy issues
• Content Gaps: Search index problems, permission mismatches, and indexing delays

Script

Hook: every deployment hits bumps

No Copilot deployment goes perfectly on day one. Users report Copilot isn’t showing up. Features work in one app but not another. Content that should be findable isn’t being surfaced.

These issues are predictable. The same problems appear in deployment after deployment, whether it’s a 50-person pilot or a 10,000-user rollout. Knowing the top 10 issues and their fixes turns hours of confusion into minutes of resolution.

Let’s walk through each category.

Licensing and assignment issues

Licensing problems are the number one cause of “Copilot isn’t working.”

The most common issue: Copilot doesn’t appear in a user’s apps. The first thing to check is whether the user has both a qualifying base license and the Copilot add-on. Go to the Microsoft 365 admin center, navigate to Users, then Active users, select the user, and check Licenses and apps. You need to see both Microsoft 365 E3 or E5 and Microsoft 365 Copilot assigned.

If you’re using group-based licensing, check the group’s license assignment status for errors. Common errors include “not enough licenses”—you’ve assigned more users to the group than you have licenses available—and “conflicting service plan”—the user has another license that includes a service plan that conflicts with Copilot.

License propagation delay catches many admins. After assigning a Copilot license, it can take up to 24 hours for Copilot features to appear in the user’s apps. This is normal. If someone reports that Copilot isn’t showing up and the license was assigned today, the fix is to wait. Check again tomorrow.

Conflicting service plans are less common but harder to diagnose. If a user has multiple Microsoft 365 licenses with overlapping service plans, some combinations create conflicts that prevent Copilot from activating. The admin center shows conflicts on the user’s license page—look for warning icons or error messages. Resolution usually involves removing the conflicting license or adjusting the service plan assignments.

App version and client issues

Copilot requires current versions of Microsoft 365 apps. If a user’s apps are outdated, Copilot won’t appear even with a valid license.

The most common version problem: the user is running a perpetual Office version—Office 2019, Office 2021, or Office LTSC. These versions do not support Copilot and never will. The user must be migrated to Microsoft 365 Apps for Enterprise.

Update channel matters. Copilot features are delivered through the Current Channel and Monthly Enterprise Channel. If your organization is on the Semi-Annual Enterprise Channel, Copilot features may arrive later. Verify your update channel in any M365 app: File, then Account, then the update channel is displayed under Product Information.

Web app versus desktop app: Copilot is available in both, but the feature set may differ. If a user reports features missing in the web app that they see on desktop, or vice versa, check whether the feature is supported on that platform.

Mobile client support exists but with limitations. Copilot on mobile devices has a different feature set than desktop or web. Set expectations with your users about what’s available on each platform.

The fix for most client issues: ensure users are on Microsoft 365 Apps for Enterprise, Current Channel or Monthly Enterprise Channel, version 2309 or later. Push updates before enabling Copilot licenses.

Network and connectivity problems

If Copilot can’t reach Microsoft’s services, it won’t function. And in government environments with restrictive network configurations, this is a frequent issue.

Blocked endpoints are the most common network problem. Copilot requires connectivity to specific Microsoft service endpoints. If your proxy or firewall blocks these endpoints, Copilot features either won’t appear or will appear but fail when used. Check your proxy logs for blocked connections to Microsoft Graph, substrate, and Copilot-specific endpoints.

SSL inspection interference. Government networks often inspect encrypted traffic. SSL inspection on Microsoft 365 “Optimize” and “Allow” endpoints can break Copilot’s communication with backend services. If Copilot is intermittently failing or returning errors, SSL inspection is a prime suspect. Bypass inspection for M365 endpoints and test again.

Government-specific endpoint mistakes. This is a common and avoidable error. GCC, GCC High, and DoD each have different endpoint lists. If you’re using the commercial endpoint list for a GCC High tenant, or the GCC list for a DoD tenant, your traffic is being sent to the wrong infrastructure. Use the endpoint list specific to your cloud environment.

VPN split tunneling. If your users connect through VPN, verify that Microsoft 365 traffic is configured for split tunneling—routing directly to Microsoft’s endpoints rather than through your VPN concentrator. Tunneling M365 traffic through VPN adds latency and can cause Copilot timeouts.

Configuration and policy conflicts

Sometimes the issue isn’t licensing or network—it’s that an admin setting is blocking Copilot.

Conditional Access conflicts. A Conditional Access policy that blocks unmanaged apps, restricts specific cloud apps, or enforces aggressive session controls can prevent Copilot from functioning. Use the “What If” tool in the Entra admin center to simulate a user’s sign-in and identify which policies are applying. Adjust policies that inadvertently block Copilot.

Tenant-level Copilot disabled. In the Microsoft 365 admin center under Settings, then Copilot, verify that Copilot is enabled at the tenant level. If a previous admin disabled it during testing and didn’t re-enable it, no users will see Copilot regardless of licensing.

App-specific policies. Copilot can be disabled for specific apps. If a user sees Copilot in Teams but not in Word, check whether Copilot in Word has been disabled in the admin settings. These are separate toggles.

Web grounding misconfiguration. If web grounding is disabled but users expect web-enhanced responses, they’ll report that Copilot doesn’t know current information. This isn’t a bug—it’s the configured behavior. Make sure users understand what Copilot can and can’t access based on your policy decisions.

Content and data access issues

Users expect Copilot to find everything. When it doesn’t, they report it as broken.

Copilot can’t find organizational content. The first question: can the user find the content directly through SharePoint search? If not, Copilot can’t either. The issue is with the search index, not Copilot. Run a SharePoint search health check.

SharePoint search index gaps. If sites or content have been excluded from the search index—intentionally or accidentally—that content is invisible to Copilot. Review your search configuration for excluded paths and URLs. If content was recently migrated or created, the search crawler may not have processed it yet.

Permission mismatches. A user complains that Copilot can’t access a document they know exists. But does the user actually have permission to that document? Copilot respects existing permissions. If the user can’t access the content directly, Copilot can’t surface it. This is the security model working as designed.

Semantic Index not yet built. In the first days after Copilot deployment, the Semantic Index is still building. Copilot’s ability to find and understand organizational content improves over time. If users report that Copilot “doesn’t know anything about our organization” during the first week, the answer is often: give it time.

Close: the quick-fix reference card

Here’s your top 10 quick-fix reference.

One: Copilot not appearing. Check both base and add-on licenses. Two: Still not appearing after licensing. Wait 24 hours for propagation. Three: License assigned but Copilot button missing. Update to current M365 Apps version. Four: Copilot loads but fails with errors. Check proxy and firewall for blocked endpoints. Five: Intermittent failures. Check SSL inspection on M365 endpoints.

Six: Copilot works in Teams but not Word. Check app-specific admin settings. Seven: Conditional Access blocking users. Run “What If” analysis and adjust policies. Eight: Can’t find organizational content. Check SharePoint search health. Nine: Content exists but Copilot doesn’t see it. Verify user permissions to the content. Ten: Copilot responses seem limited. Check web grounding settings and Semantic Index maturity.

Two rules of thumb. If the issue appeared within 24 hours of a change, wait before troubleshooting—propagation may be in progress. If the same issue affects multiple users, it’s a configuration problem, not a user problem.

Build an internal knowledge base. Every issue you resolve, document the symptoms, the diagnosis, and the fix. Over time, this becomes your team’s most valuable support resource.

Sources & References

• Microsoft 365 Copilot setup — Setup guidance with common pitfalls
• Enable users for Microsoft 365 Copilot — User enablement and troubleshooting
• Microsoft 365 Copilot help — End-user support and known issues